Love the comment about Baby Mine from Dumbo.

Hi, Kegz-people. Long-time lurker, first-time poster. Here's two: "Stretched on Your Grave", Dead Can Dance (cover); "I Know", Fiona Apple. The latter's a somewhat ironic choice, as the composer has called it the happiest song she's written.

Many good choices on the list and here, and since i am a big fan of the sad song here are some suggestions: "Providence" by Sonic Youth, "Here Comes the Flood" by Peter Gabriel, "Sunken Treasure" by Wilco, "Nobody Home" by Pink Floyd, "Winona" by Matthew Sweet.

And "X-Factor" by Lauryn Hill. DANGity dang dang it makes me want to sob my eyes out.

I have to add "Sympathy" by Sleater-Kinney. Written by lead singer Corin when her daughter was born a premie. Maybe not THE saddest song ever but it always tugs on my heart strings. As does "The Remainder."

Her son! I meant her son! (Hm, more slips re: that I think you guys are having a girl?)

"Last Kiss" by Wayne Cochran
"No Woman, No Cry" by Bob Marley

i hate country but the saddest song ever is concrete angel by martina mcbride! ITS SO SAD!